113886-71-8

Basic information

• Product Name: N4-Acetyl-2'-O-Methyl-cytidine
• Synonyms: N4-Acetyl-2'-O-Methyl-cytidine;Ac-2'-OMe-C;N-Acetyl-2'-O-methylcytidine;Cytidine,N-acetyl-2'-O-methyl-;Cytidine,N-acetyl-2'-O-methyl-
• CAS NO: 113886-71-8
• Molecular Formula: C12H17N3O6
• Molecular Weight: 299
• EINECS: 1312995-182-4
• Mol File: 113886-71-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.58±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• PKA: 10.20±0.20(Predicted)
• CAS DataBase Reference: N4-Acetyl-2'-O-Methyl-cytidine(CAS DataBase Reference)
• NIST Chemistry Reference: N4-Acetyl-2'-O-Methyl-cytidine(113886-71-8)
• EPA Substance Registry System: N4-Acetyl-2'-O-Methyl-cytidine(113886-71-8)

Safety Data

• Hazardous Substances Data: 113886-71-8(Hazardous Substances Data)

Usage

Uses

N4-Acetyl-2’-O-methyl-cytidine is a useful compound in the synthesis of functionalized oligonucleotides.

Upstream product

• 108-24-7 acetic anhydride 
• 2140-72-9 2'-O-methylcytidine 
• 3768-18-1 N-acetylcytidine 
• 85335-73-5 N₄-acetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)cytidine 
• 10212-28-9 2,2'-anhydro-1-(β-D-arabinofuranosyl)cytosine acetate 
• 199593-14-1 N-[2-Oxo-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,2-dihydro-pyrimidin-4-yl]-acetamide 
• 18968-50-8 1-[6-methoxy-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro-[2,3-d][1,3]dioxol-5-yl]-(1R)-ethane-1,2-diol 
• 133120-44-2 N-(2-Oxo-1-trimethylsilanyl-1,2-dihydro-pyrimidin-4-yl)-acetamide 

Downstream Products

• 199593-09-4 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 

Relevant articles and documents

Improved synthetic approaches toward 2'-O-methyl-adenosine and guanosine and their N-acyl derivatives

We developed several improved approaches toward 2'-O-methyl adenosine and guanosine and their N-acyl derivatives. (a) Transglycosylation of N4- acetyl-5', 3'-di-O-acetyl-2'-O-methyl cytidine with N6-Bz-adenine provided N6-benzoyl-5'3'-di-O-acetyl-2'-O-methyl adenosine in 50% yield. (b) Regioselective methylation of 2-amino-6-chloro purine riboside with MeI/NaH followed by hydrolysis provided 2'-O-Me-guanosine in high yield. The same 2'- O-Me-precursor was transformed into 2'-O-Me-adenosine in 58% yield. (c) Very efficient transformation of 2,6-diamino-purine riboside into N2-isobutyryl (isopropylphenoxyacetyl) 2'-O-Me-guanosine through methylation of 5',3'-O- TIPDSi derivative followed by selective N2-acylation, deamination and desylilation provided target compounds in 70% combined yield. (d) Mg2+ and Ag+ directed methylation of N1-Bzl-guanosine proceeded in >80% yield with ratio of 2'-O-Me-3'-O-Me=9:1. The same methylation of adenosine with Ag+ and Sr2+ acetylacetonates provided 2'-O-Me-adenosine in 75-80% yield. (C) 2000 Elsevier Science Ltd.

Alternate approaches to the synthesis of 2'-O-Me nucleosides

Three different approaches to the synthesis of 2'-O-methyl nucleosides starting from the corresponding nucleoside or commercially available 1,2:5,6-di-O-isopropylidene-α-D-allofuranose 1 are described.